Synthesis of new benzotriazepin-5(2H)-one derivatives of expected antipsychotic activity

Medicinal Chemistry Research

Volumn 22, Issue 3, 2013, Pages 1488-1496

  Ibrahim, Samy M ^a   Baraka, Mohamed M ^a   El Sabbagh, Osama I ^b   Kothayer, Hend ^a  

^a Zagazig University   (Egypt)

^b TAIF UNIVERSITY   (Saudi Arabia)

Author keywords

Antipsychotic activity; Benzotriazepin 5(2H) one; Clozapine; Synthesis

Indexed keywords

1 METHYL 2,3 DIPHENYL 3,4 DIHYDRO 1H BENZO[E][1,2,4]TRIAZEPIN 5(2H) ONE; 1 METHYL 3 PHENYL 2 THIOXO 3,4 DIHYDRO 1H BENZO[E][1,2,4]TRIAZEPIN 5(2H) ONE; 1 METHYL 3 PHENYL 3,4 DIHYDRO 1H BENZO[E][1,2,4]TRIAZEPIN 5(2H) ONE; 1,3,4 BENZOTRIAZEPINE DERIVATIVE; 2 (2 NITROPHENYL) 1 METHYL 3 PHENYL 3,4 DIHYDRO 1H BENZO[E][1,2,4]TRIAZEPIN 5(2H) ONE; 2 (3,4,5 TRIMETHOXYPHENYL) 1 METHYL 3 PHENYL 3,4 DIHYDRO 1H BENZO[E][1,2,4]TRIAZEZPIN 5(2H) ONE; 2 (4 BROMOPHENYL) 1 METHYL 3 PHENYL 3,4 DIHYDRO 1H BENZO[E][1,2,4]TRIAZEPIN 5(2H) ONE; 2 (4 CHLOROPHENYL) 1 METHYL 3 PHENYL 3,4 DIHYDRO 1H BENZO[E][1,2,4]TRIAZEPIN 5(2H) ONE; 2 (4 HYDROXPHENYL) 1 METHYL 3 PHENYL 3,4 DIHYDRO 4H BENZO[E][1,2,4]TRIAZEPIN 5(2H) ONCE; 2 (4 METHOXYPHENYL) 1 METHYL 3 PHENYL 3,4 DIHYDRO 1H BENZO[E][1,2,4]TRIAZEPIN 5(2H) ONE; 2 (4 NITROPHENYL) 1 METHYL 3 PHENYL 3,4 DIHYDRO 1H BENZO[E][1,2,4]TRIAZEPIN 5(2H) ONE; 2 (METHYLAMINO) N' PHENYLBENZOHYDRAZIDE; 3 ISONICOTINOYL 1 METHYL 3,4 DIHYDRO 1H BENZO[E][1,2,4]TRIAZEPIN 5(2H) ONE; ALDEHYDE; CARBON DISULFIDE; CLOZAPINE; FORMALDEHYDE; HYDRAZINE DERIVATIVE; NEUROLEPTIC AGENT; UNCLASSIFIED DRUG;

ACIDITY; ALKALINITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CENTRAL NERVOUS SYSTEM DEPRESSION; CONTROLLED STUDY; DRUG SAFETY; DRUG SYNTHESIS; FORCED SWIMMING TEST; MALE; MOUSE; NEUROTOXICITY; NONHUMAN; POLYMERIZATION; PTOSIS; ROTAROD TEST;

EID: 84874118932     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0102-2     Document Type: Article

References (17)

1. Britton TC, Trepanier DL (1980) Method for preparing 6-phenyl-triazolo or imidazolo-(1,3,4)-benzotriazepines and the novel intermediates used therewith. US Patent, 4, 189, 588
2. Chen G, Bohner B (1965) Cited in screening methods in pharmacology, 1st edn. Academic Press, New York, p 182
3. Coughenour LL, Mclean JR, Parker RB (1977) A new device for the rapid measurement of impaired motor function in mice. Pharmacol Biochem Behav 6:351-353
4. Dunham NW, Miya TS (1957) A note on a simple apparatus for detecting neurological deficit in rats and mice. J Am Pharm Assoc Sci Ed 46:208-209
5. Fernándeza P, Guille′n MI, Gomarc F, Aller E, Molina P, Alcaraz MJ (2004) A novel cyclo-oxygenase-2 inhibitor modulates catabolic and antiinflammatory mediators in osteoarthritis. Biochem Pharmacol 68:417-421
6. Fischer R, Künzle FM, Schmuz J (1984) Pyrrolobenzotriazepines. US Patent 4, 450, 108
7. Fisher RS (1989) Animal models of the epilepsies. Brain Res Rev 14:245-278
8. Kaur K, Talele TT (2008) D QSAR studies of benzotriazepine derivatives as CCK receptor antagonists. J Mol Graph Model 27:409-420
9. Kim SH, Taylor JE (1992) 2H-1,3,4-benzotriazepin-2-ones. US Patent 5, 091, 381
10. Legrand L, Lozac'h N (1984) Heterocyclic sulfur compounds. CIII. Effect of phenylhydrazine on 1,2-dihydro-3,1-benzothiazine-4-thiones. J Heterocycl Chem 21:1625-1632
11. Mao QQ, Ip SP, Tsai SH, Che CT (2008) Antidepressant-like effect of peony glycosides in mice. J Ethnopharmacol 119:272-275
12. Osonoe K, Mori N, Suzuki K, Osonoe M (1994) Antiepileptic effects of inhibitors of nitric oxide synthase examined in pentylenetetrazol induced seizures in rats. Brain Res 663:338-340
13. Pestellini V, Ghelardoni M, Volterra G, Del Soldato P (1978) Anti-inflammatory and antalgic activity of fused ring polycyclic compounds: 2,10-dioxo-pyridazino[3,2-b]quinazolines. Eur J Med Chem 13:296
14. Porsolt RD, Anton G, Blavet N, Jalfre M (1978) Behavioural despair in rats: a new model sensitive to antidepressant treatments. Eur J Pharmacol 47:379-391
15. Reddy PSN, Reddy PP (1988) Reaction of 2-aminobenzoylhydrazines with carboxylic acids: formation of quinazolin-4(3H)-one, 1,3,4-oxadiazole and 1,3,4-benzotriazepin-5-one derivatives. Indian J Chem, Sect B 27B:763-765
16. Schuler E, Juanico N, Teixido J, Michelotti EL, Borrell JI (2006) A diversity oriented synthesis of 2,10-dioxo-10H-1,2,3,4,4a,5- hexahydropyridazino[3,2-b]quinazolines. Heterocycles 67:161-173
17. Spencer J, Gaffen J, Griffin E, Harper EA, Linney ID, McDonald IM, Roberts SP, Shaxted ME, Adatia T, Bashall A (2008) Achiral, selective CCK2 receptor antagonists based on a 1,3,5-benzotriazepine-2,4-dione template. Bioorg Med Chem 16:2974-2983